[n]Cyclo‐2,7‐naphthylenes: Synthesis and Isolation of Macrocyclic Aromatic Hydrocarbons having Bipolar Carrier Transport Ability

Abstract

Mottenkugel‐Makrocyclen: Naphthalin wurde zu makrocylischen Oligomeren aus fünf, sechs und sieben Naphthalineinheiten gekuppelt (siehe Bild). Die thermisch stabilen Makrocylen mit 50, 60 oder 70 π Elektronen in reinen Kohlenwasserstoffen bilden im Kristall säulenförmige Assoziate und dienen als bipolare Transportmaterialien für Träger in organischen Leuchtdioden.

[6]Cyclo-2,7-naphthylene: a redetermination

“…Superior quality crystals of the title compound were obtained by re-optimizing the crystallization conditions. For the synthesis and preceding crystallographic analysis, see: Nakanishi et al (2011). For the original method of recrystallization, see: Miyahara & Shimizu (2001).…”

“…We thank Professor T. Iwamoto for the use of the X-ray instrument. Nakanishi et al, 2011). The unique macrocyclic structures of [n]CNAPs (n = 5, 6 and 7) were revealed by X-ray crystallographic analysis of the single crystals, but we deferred detailed discussion of the most abundant compounds,…”

“…Single crystals of a macrocyclic hydrocarbon, [6]cyclo-2,7naphthylene ([6]CNAP, C 60 H 36 ) were prepared from anthracene melt with a prolonged time for the recrystallization. The crystal of improved quality led to the correction of the spacegroup assignment to Cmca from P1 in the original determination [Nakanishi et al (2011) Angew. Chem.…”

Spin Transport in Magnetic Tunnel Junctions with the Insertion of [6]Cyclo-2,7-naphthylenes Organic Semiconductor

“…In this study we investigate the spin-dependent transport property of magnetic junctions including [6]cyclo-2,7naphthylenes (CNAP) [9]. An illustration of molecular structure of CNAP is shown in Fig.…”

Macrocyclic Restriction with Flexible Alkylene Linkers: A Simple Strategy to Control the Solid‐State Properties of π‐Conjugated Systems

“…[2] Construction of a macrocyclic structure is also a promising design for controlling the assembly of the p skeleton, in which the construction of shape-persistent p skeleton is crucial, as their rigid and planar skeletons, such as cyclic oligo(aryleneethynylene)s, are beneficial to forming a one-dimensional assembly through effective p-p stacking interactions. [3] A variety of non-shape-persistent macrocycles consisting of two or more p skeletons connected with flexible linkers have also been synthesized. However, the interest of those studies is mainly to elucidate the intramolecular interaction among the p moieties, [4] and guest-binding behavior in the central cavity, [5] or to establish the ring-opening polymerization methodology, [6] but not to control the molecular alignment in the solid state.…”